Toronto sprawls along the northern shore of Lake Ontario, its pulsating centre encased by a jangle of satellite townships and industrial zones which cover – as the Greater Toronto Area (GTA) – no less than one hundred square kilometres. In recent decades, successive city administrations and a raft of wealthy benefactors have lavished millions of dollars on glitzy architecture, slick museums, an excellent public transport system and the reclamation and development of the lakefront. As a result, few would argue that Toronto has become the cultural and economic focus of English-speaking Canada, and its five and a million inhabitants share what must surely be one of North America’s most likeable, liveable cities.

The city has its share of attention-grabbing places to visit and the majority are conveniently clustered in the centre – either Downtown or Uptown. The most celebrated of them is the CN Tower, until recently the world’s tallest freestanding structure, which stands next to the modern hump of the SkyDome stadium, now the Rogers Centre. The city’s other prestige attractions kick off with the Art Gallery of Ontario, which possesses a first-rate selection of Canadian painting, and the Royal Ontario Museum, where pride of place goes to the Chinese and aboriginal peoples collections. Yet it’s the pick of Toronto’s smaller galleries that really add to the city’s charm. There are a superb collection of ceramics at the Gardiner Museum, a fascinating range of footwear at the Bata Shoe Museum and the small but eclectic Gallery of Inuit Art owned by the Toronto Dominion Bank. You’ll find absorbing period homes too, most memorably the mock-Gothic extravagances of Casa Loma and the Victorian gentility of Spadina House, as well as the replica colonial fortress of Fort York, where Toronto began. Spare some time also for the good-looking buildings of the lively St Lawrenceneighbourhood and the Distillery District, the city’s brightest arts and entertainments complex, sited in a capacious former distillery. Indeed, there is an outstanding programme of performing arts, from dance to theatre and beyond, as well as exciting festivals, a vibrant club scene and literally hundreds of cafés and restaurants.

Toronto’s sights illustrate different facets of the city, but in no way do they crystallize its identity. The city remains opaque, too big and diverse to allow for a defining personality and this, of course, adds an enticing air of excitement and unpredictability to the place. Neither is its layout predictable: Toronto may have evolved from a lakeside settlement, but its growth has been sporadic and mostly unplanned, resulting in a cityscape that can seem a particularly random mix of the old and the new. This apparent disarray, when combined with the city’s muggy summers, means most visitors spend their time hopping from sight to sight on the transit rather than walking. Yet, if you’ve the time and determination to get under the skin of the city, take to your feet and Toronto will slowly reveal itself.

Brief history

Situated on the slab of land separating Lake Ontario and Georgian Bay, Toronto was on one of the early portage routes into the interior, its name taken from the Huron for “place of meeting”. The first European to visit the district was the French explorer Étienne Brûlé in 1615, but it wasn’t until the middle of the eighteenth century that the French made a serious effort to control Lake Ontario with the development of a simple settlement and stockade, Fort Rouillé. The British pushed the French from the northern shore of Lake Ontario in 1759, but then chose to ignore the site for almost forty years until the arrival of hundreds of United Empire Loyalists in the aftermath of the American Revolution.

In 1791 the British divided their remaining American territories into two, Upper and Lower Canada. The first capital of Upper Canada was Niagara-on-the-Lake, but this was too near the American border for comfort and the province’s new lieutenant-governor, John Graves Simcoe, moved his administration to the relative safety of Toronto in 1793, calling the new settlement York. Simcoe had grand classical visions of colonial settlement, but was exasperated by the conditions of frontier life, noting “the city’s site was better calculated for a frog pond … than for the residence of human beings”. Nicknamed “Muddy York”, the capital was little more than a village when, in 1812, the Americans attacked and burnt its main buildings.

The Family Compact – and William Lyon Mackenzie

In the early nineteenth century, effective economic and political power lay in the hands of an anglophile oligarchy christened the Family Compact by the radical polemicists of the day. The Compact’s most vociferous opponent was a radical Scot, William Lyon Mackenzie, who promulgated his views both in his newspaper, the Colonial Advocate, and as a member of the legislative assembly. Mackenzie became the first mayor of Toronto, as the town was renamed in 1834, but the radicals were defeated in the elections two years later and a frustrated Mackenzie drifted towards the idea of armed revolt. In 1837, he staged a poorly organized insurrection, during which a few hundred farmers marched down the main drag, Yonge Street, fought a couple of half-hearted skirmishes and then melted away. Mackenzie fled across the border and two of the other ringleaders were executed, but the British parliament, mindful of similar events that led to the American Revolution, moved to liberalize Upper Canada’s administration instead of taking reprisals. In 1841, they granted Canada responsible government, reuniting the two provinces in a loose confederation, prefiguring the final union of 1867 when Upper Canada was redesignated Ontario.

Toronto the Good

By the end of the nineteenth century, Toronto had become a major manufacturing centre dominated by a conservative mercantile elite, which was exceedingly loyal to the British interest and maintained a strong Protestant tradition. This elite was sustained by the working-class Orange Lodges, whose reactionary influence was a key feature of municipal politics, prompting a visiting Charles Dickens to complain about the city’s “rabid Toryism”. Other commentators were equally critical, referring to Toronto at one time or another as “Hogtown” and – with more than a slice of irony – “Toronto the Good”. Nevertheless, these same Protestants were enthusiastic about public education, just like the Methodist-leaning middle classes, who spearheaded social reform movements, principally suffrage and temperance. The trappings, however, remained far from alluring – well into the twentieth century Sunday was preserved as a “day of rest” and Eaton’s store drew its curtains to prevent Sabbath window-shopping. Indeed, for all its capital status, the city was strikingly provincial by comparison with Montréal until well into the 1950s, when the opening of the St Lawrence Seaway gave the place something of a jolt and the first wave of non-white immigrants began to transform the city’s complexion.

Modern Toronto

In the 1960s, the economy exploded, and the city’s appearance was transformed by the construction of a series of mighty, modernistic skyscrapers. This helter-skelter development was further boosted by the troubles in Québec, where the clamour for fair treatment by the francophones prompted many of Montréal’s anglophone-dominated financial institutions and big businesses to transfer to Toronto. Since then, Toronto’s economy has followed the cycles of boom and retrenchment common to the rest of the country, but politically Ontario took a turn to the right in the mid-1990s with the election of the Progressive Conservatives led by Mike Harris. Nothing if not hard-nosed, Harris pushed through a major governmental reorganization, combining the city of Toronto with its surrounding suburbs to create the “Mega City” of today. The change was deeply unpopular in Toronto itself, but Harris still managed to get himself re-elected in 2000 with the large-scale support of small-town and suburban Ontario. In 2003, Ontario returned to the political centre, ejecting the Progressive Conservatives in favour of the Liberals, heralding a move towards more moderate, consensual politics; the Liberals remain in power at time of writing.

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Toronto’s neighbourhoods

One of Toronto’s most striking features is its division into distinct neighbourhoods, many of them based on ethnic origin, others defined by sexual preference or indeed income. Bilingual street signs identify some of these neighbourhoods, but architecturally they are often indistinguishable from their surroundings. The following rundown will help you get the most from the city’s demographic mosaic, whether you want to shop, eat or just take in the atmosphere. But bear in mind that there is a certain artificiality in the nomenclature: Chinatown, for instance, has hundreds of Vietnamese residents, Little Italy many Portuguese.

The Beaches

South of Queen Street East between Woodbine and Victoria Park Ave. A prosperous and particularly appealing district with chic boutiques, leafy streets and a sandy beach trimmed by a popular boardwalk.

Cabbagetown

East of Jarvis and roughly bounded by Gerrard Street East on its south side, Wellesley to the north and the Don River to the east. Noted for its trim Victorian housing, the name comes from the district’s nineteenth-century immigrants, whose tiny front gardens were filled with cabbages. Locals even cultivate their own community flag.

Chinatown

Spreads west along Dundas Street West from Beverley and then north up Spadina to College. This is one of Toronto’s most distinctive neighbourhoods, crowded with busy restaurants and stores selling anything from porcelain and jade to herbs and pickled seaweed.

The Gay Village

The Village’s plethora of bars, restaurants and bookshops zero in on the intersection of Church and Wellesley streets. Jammed to the gunnels during Toronto Pride held in the last week of June.

Kensington Market

Just north of Dundas between Spadina and Augusta. Perhaps the most ethnically diverse part of town, combining Portuguese, West Indian and Jewish Canadians, who pack the streets with a plethora of tiny shops and open-air stalls.

Little Italy

The so-called Corso Italia, which runs along College between Bathurst and Ossington, is one of Toronto’s liveliest neighbourhoods, with a gaggle of good restaurants and bars.

Little Portugal

A crowded, vital area packed with shops and neighbourhood food joints, focused on Dundas Street West from Ossington to Lansdowne Ave.

Queen West

Queen Street West, between University and Spadina, was once the grooviest part of town, but rising rents have long since pushed its crew of uber-cool Torontonians further west to what is often called “West Queen West”, running west from Strachan Street to Dufferin. West Queen West is the city’s star turn, with great bars, restaurants and shops.

Yorkville

Just above Bloor between Bay Street and Avenue Road, Yorkville was “alternative” in the 1960s, with regular appearances by the leading lights of the counterculture like Gordon Lightfoot and Joni Mitchell. Today, the alternative jive is long gone, and the district holds some of Toronto’s most chi-chi clothing shops and art galleries.

Toronto’s leading festivals

The Toronto International Film Festival or TIFF (w tiff.net) is one of the most respected film festivals in the world – and the largest in North America. A ten-day affair, the festival begins on the first Thursday in September and queues to get into the films can be fearsome. Single, same-day tickets are available from the Film Festival’s box offices (or as rush tickets immediately before screenings), but regular TIFF attendees mostly buy books of tickets in advance – a somewhat more economical method – or opt for one of several passes, which can be purchased from the TIFF website. In all cases, book well ahead. In June, there’s the outstanding Toronto Jazz Festival (w tojazz.com), which usually overlaps with the week-long Gay & Lesbian Pride (w pridetoronto.com), culminating in a whopping Pride Day Parade.

Accommodation

The bulk of the city’s hotels occupy modern skyscrapers, though the opening of a string of boutique hotels in the last few years has livened things up considerably. Availability can be a problem, especially during the city’s big festivals, but booking in advance is recommended at any time of the year. Prices fluctuate wildly, but in general double rooms in the city centre start at about $140. Bed and breakfast accommodation tends to be less expensive and although most of these establishments are not as central as the city’s hotels, they often take you out into Toronto’s quainter/quieter neighbourhoods. Budget-conscious travellers might want to consider one of the city’s hostels or opt instead for a student room in one of the university’s halls of residence, available – with some variation – from the second week in May to late August. The Ontario Tourism travel information centre will help in finding a hotel room, as will Tourism Toronto.

Eating and drinking

Toronto simply heaves with cafés and restaurants – everything from smart and expensive designer places to informal neighbourhood joints. Some of the best emphasize their use of Canadian ingredients – fish and wild game, particularly – but there’s no real distinctive local cuisine per se. Prices range from upwards of $60 for a meal at fancier restaurants, to bargain-basement cafés where a decent-sized snack or sandwich works out at just a few dollars. The majority of places fall somewhere in between – a $35 bill per person for a two-course meal, excluding drinks, is a reasonable average in a restaurant. For drinking, many of Toronto’s traditional bars are rough-and-ready places that look and feel like beer halls – no wonder most locals prefer to drink where they eat. Indeed, until the 1980s, it was common for most of the city’s bars to have one entrance for men accompanied by women, the other for men only, and although these niceties have been stripped away, many of them remain firmly blue collar; others – and these are the pick – feature a wide range of “craft” beers from any number of small and emergent breweries, others concentrate on live music and yet more have morphed into clubs. Nearly all of them serve (bar) food of some description or other.

Nightlife and entertainment

Toronto has a flourishing live music scene both for big-name and up-and-coming bands and artists and jazz is well represented too. The club scene is also vibrant, if not exactly earth-shattering, but there’s more than enough to keep anyone going for days (and nights) on end. For listings, consult NOW (w nowtoronto.com), a free weekly magazine widely available around town. As for the performing arts, Toronto sustains a wide-ranging programme of theatre, opera, ballet and classical music. Its particular strength is its theatre scene, the third-largest in the English-speaking world, after London and New York. For film, Toronto’s mainstream cinemas show Hollywood releases before they reach Europe and the city has an excellent art-house cinema – as befits a city that hosts what is often regarded as the world’s best film festival, the renowned Toronto International Film Festival.